The Oral History of Okayplayer

The birth of the hip-hop website that started it all.

It’s hard to believe now, considering the horde of followers he’s amassed on Twitter (2.4 million strong and growing), but when the Internet first started popping off, Ahmir “Questlove” Thompson thought the revolution would be televised. Yes, if it wasn’t for a headstrong, witty, University of Pennsylvania student named Angela Nissel, Questo—the most famous drummer in the world and the most visible member of The Roots—might have stuck with WebTV and would never have gone on to found Okayplayer. And that would have been a shame because the site basically laid the foundation for most modern music blogs and shaped the way we discuss rap on the Internet.

Today OKP is based in NYC, and has expanded into a record label that produces live events. The site now boasts a tab called LNWJF that houses videos from The Roots’ performances on NBC’s Late Night With Jimmy Fallon, and affiliated specialist sites like the Revivalist for jazz, OkayAfrica for African music, the reggae site LargeUp, and Okayfuture, the newly launched site for electronic with hip-hop and soul aesthetics. There’s no denying it—Okayplayer is kinda major. But what we’re about to do right here is go back—all the way back.

Like most startups, Okayplayer began humbly—in Questlove’s Philadelphia bedroom, to be specific. In the beginning Okayplayer had no particular mission beyond chronicling the everyday dealings of all things The Roots. The site expanded to create lanes for various associated acts—of which there were many. But there were no advertisers and no suggestion of a road to profitability. This was a labor of love that grew into one of the most influential websites ever created. The web crew, like the band, was small, consisting of Questo, two programmers named Doug Muir and Shawn Gee, and, Angela, the “web mistress” and de facto editor, who birthed the site’s identity and distinctively irreverent voice.

Launched in 1999—four years before MySpace, five years before Facebook, and seven years before Twitter—Okayplayer was one of the first places where fans could interact directly with artists without a PR filter. The thrill of real-time interaction proved to be a powerful draw. In addition to its daily blog updates, the most popular part of Okayplayer, inspiring the love and ire of rappers and singers far and near, were the message boards. They attracted a motley crew of informed, sharp, and, at times hilarious hip-hop heads who would spit the most acrid of vitriol when provoked (often cloaked in a patina of positivity and “consciousness”). It didn’t matter if it was a fellow message board member or a rapper whose video had just graced Rap City—anybody could get it.

The web is now littered with music sites—some of which boast larger followings, more pageviews, and even bigger name backers. But none has had the formative impact that Okayplayer exerted on the culture. Think of it this way: Besides Reddit, what other site attracted a readership that feels enough like kin to have a yearly meet-up? But how did this site that angered Tweli Kweli enough to name drop it on song come to be? We let the people who were there from jump tell the story in their own words.

THE BEDROOM

Questlove: After high school, I couldn’t afford to go to Juilliard. At the time, I took off a year and a half to work at an insurance company that was paying significant money so I could save for college. This was back in ’89 / ’90. By that point, I had met my partner Angela Nissel who was a creative writing major at the high school I had just graduated from [Philadelphia High School for the Creative and Performing Arts]. We maintained an on-and-off friendship in that time period. She went to University of Pennsylvania. I would see her during The Roots’ struggling days.

Black people discovering technology is such a truly hilarious, albeit primitive, experience to observe. I was one of the suckers that purchased WebTV, which basically lets you surf on the Internet via your television. The same way that Angela wanted to smack me on the back of the head for not having a computer is the same way I’m trying to smack cats now—like half the cats that you see on Twitter now.

Black people discovering technology is such a truly hilarious, albeit primitive, experience to observe. —Questlove

By this point it’s 1997/1998—and surfing the “super information highway,” I would often go to the pages of bands that we toured with and bands that I liked and the only messages on their web sites were a weekly message to their fans. You know, I went to the Fugees page and it wasn’t even halfway updated from The Score. The only information I got that I didn’t know from reading magazines was Q-Tip’s spaghetti and clam recipe on the Tribe Called Quest page.

The first time I ever saw a chat-room board, it was Michael Stipe and Courtney Love fans having a debate about Roxy Music. I was fascinated. And I was like, “Wait a minute: Courtney and Michael Stipe can go real time to their fanbase, but on the hip-hop side of things, I only know that Manhattan clam chowder is the special ingredient to Q-Tip’s spaghetti recipe? I wanted to change all that.

Shawn Gee: Me and Ahmir sat down and said we want to build a Roots website. Back then there was no real business plan. It was more of an advertisement for the albums and shows. We wanted to go after TheRoots.com, which was the obvious name for the site, but a fan had already taken it and built a fanpage.

Questlove: I’d never even bothered to see if there was anything about The Roots online. One day, I searched and saw that someone had put up a Roots fan page—real primitive graphics and stuff. I actually got involved in that board, trying to answer questions, and I kind of got my feet wet giving updates and things like that on this website.

Shawn Gee: We started the negotiation with that fan and from the very beginning they were interested in selling it. But we saw early on that it was going to be a long, drawn-out process—the lawyers were going to have to get involved and everything.

Dan Petruzzi: They had been putting the Okayplayer logo on albums for years. It was really Quest’s desire to have a platform to promote his music and the band’s music and also to connect with fans of the Roots and fans of music, cause he’s a super true music head, and he knows that people who are fans of the Roots are also really into music.

Shawn Gee: Ahmir came up with the name Okayplayer. It was sort of a brand without a concept. He liked to design the covers in classic Blue Note style. And if you look at all the early albums prior to Things Fall Apart—Illadelph Halflife, Philly Organics—there was this logo that said Okayplayer: Giving You True Notes Since 1987. Long story short, Ahmir decided: Why don’t we name our website Okayplayer.com?

Here in Philly there was a colloquialism where people said, “OK, player!” as in, “Alright, dude.” But I’m not sure if that’s where Ahmir got it from. Ironically, we were able to get TheRoots.com later on down the line, but we'd already built this Okayplayer brand.

Questlove: [The name came from] Tramp. He was an art director. Back in the days of The Source, he did a cartoon called “A View From The Underground,” back in like ’91, ’92. And he designed some of our first few album covers. He did our EP From the Ground Up, he did Do You Want More?!!!??! and he also did Illadelph Halflife.

For The Ground Up, Tramp didn’t have the logo. So he just made up the first thing that came to his head until he got the proper fonts and logos from Geffen. When he showed me the first draft of the design, he just wrote “Okayplayer” in a box. And I thought OK, that’s the most Blue Note–looking artwork font-wise and everything. So then when he turns in the proper artwork with the label stuff and everything, I didn’t like it. It lost its Blue Note appeal. I told him, put that “Okayplayer” back on and just stick the logo on the back of the record. It didn’t make sense at the time, but it just felt like it needed to be there. It wasn’t like it was a label or anything, I just wanted Okayplayer to be there. And then it literally just stuck and somehow it’s found itself onto all 15 of our records.

Its meaning of course is slang for, “Well alright,” that type of thing. We didn’t say it as much as people would have thought. It was a temporary mistake that I actually liked the visual of, and we just kept it.

Shawn Gee: Most of the artist websites that were up on the net at the time were really just digital posters for lack of a better term. You saw the homepage, you saw the tour page, you saw some advertisements for records, and you may have been able to click on some photos from back in the day, but after you went once, there was really no reason to go back. One of the things we wanted to do was build something dynamic, that would change, that would give Roots fans a reason to continually visit the site.

Questlove: One day after a concert, Angela was talking about the Internet. I said I got a computer. She’s like, “Well, what is it?” I said I had Web TV. She said that wasn’t a real computer. I said it was. We argued back and forth and finally I took her to the bedroom to show her my set-up. In my head I thought I was Matthew Broderick in War Games. I was that guy. I was into ghetto shit. I’m thinking I’m Dr. Futuristic with my drum machines and turntables.

She gave me that look. It was that look like I forgot to take out the garbage and my mom and dad would wake me up Friday morning—you know, if you walk by them you would get a smack in the head. She was like, “Oh hell no, I can’t.” I was like, “What are you talking about?” She said, “I can’t watch another person fall victim to this... Look, I just want you to trust me.”

One of the things we wanted to do was build something dynamic, that would change, that would give Roots fans a reason to continually visit the site. —Shawn Gee

I happened to tell her that I was going to invest in getting a Pathfinder. She knew I didn’t have a license. She just didn’t like where she saw my life going. She’s like, “Look, it’s asinine for you to buy a car without a license. Either you’re going to get your license or don’t get a car. But please don’t get a car and be one of these dumb rapper motherfuckers getting your boy to drive you around.”

She’s like, “Why don’t you take that money and invest in your future?” I was like, “Huh?” She was like, “Take that $15,000 you going to take to buy the car and invest in your future.” She hammered it home for like 25 minutes. Next thing I know, I’m in CompUSA with her and two of her friends from the University of Pennsylvania. She tells them, “Get me your wet dream.” She told them to buy what they wish they had. I still didn’t know what she was doing. She’s like, “I’m building you your website,” and for the next three months, my bedroom became Ivy League school central.

I didn’t even know black nerds were real. She just had them in rotation—Urkel is a dweeb, but I was like, “Wow! Brothers really can be cool and educated. How come I’ve never seen this stereotype?” It transformed me.

Shawn Gee: The site had to have a personality; it had to have a voice. A lot of the time, if you’re going to a web company that built 15 other artist’s sites, they’re usually working from a template. There’s no voice, there’s no personality. So Ahmir had a friendship with a young lady who went the Univeristy of Penn who wasn’t in the digital business—but she was a web head. She understood the dynamic of the web, she understood the community aspect. She belonged to a lot of the early digital communities. And she was a geek as well. And she was a music head. And she was a Roots fan. So it was like 1 + 1 + 1 = 1000 with her.

We had a meeting with Ang and explained to her what we were interested in doing. Instead of just hiring her to build the site, we spoke about bringing her on The Roots payroll to work in a salaried position as a web designer and host—a web mistress, I think she called it. And that was probably the first great decision made in the history of the Okayplayer, because Ang was able to give Okayplayer that personality and that voice

Questlove: My house was always a haven. It was constantly being occupied by somewhere between 10 to 15 people. We were sort of like the East Coast version of The Pharcyde Manor. First floor was where all the writers and singers were. Any lyrical ideas that had to get done, that’s where that happened. The second floor—that’s where all the tech nerds hung.

Angela asked me what I wanted from the site and I told her I wanted to build a playground where people can actually interact with me. At the point, I told her I’ll be online four hours a day. She thought that was ridiculous. She’s like, “No one is on four hours a day.” I said, “I’ll bet you I’ll be online four hours a day.” When the site first came up, I was on it six hours a day.

Shawn Gee: For the first two or three months the website was run out of Quest’s bedroom. Ang asked for a bunch of materials, we got a bunch of pictures and different things. The guys were going on a four-to-five-month tour right after Angie was hired. So we set the computer up in Ahmir’s bedroom. Ahmir gave her the keys.

Questlove’s bedroom was like a storage place with any asset you would want. Whether that was old VHS of The Roots performing or photo shoots or whatever Roots paraphernalia—it was somewhere in that bedroom. So Ang spent a lot of time going through those things and found enough assets to put together what was initially a splash page that had the graphics and images from the Things Fall Apart album.

Questlove: Slowly but surely, as I would leave the house to go to the studio to record, she would come to the house and build Okayplayer. I would like to think we finished both projects at the same time. I mastered that record [Things Fall Apart] in November of 1998 for release in February. I believe we actually went live a week and a half after the album came out. We haven’t turned back since.

Shawn Gee: When the guys were over in Europe, Ahmir would call back and give Ang updates on each show and what they were doing. Ang would type the update in real time so when someone woke up the next morning and went to OKP.com they had new information.

In these days and times a blog seems like a simple concept, but you gotta figure this is 13 years ago, where there were no blogs. It was all sort of static advertisements. That’s all websites were. It was a novel concept to have dynamic information that changed not only once a day but multiple times within a day.

Talib Kweli: In ‘99 when the site went live it was like this crazy idea. Okayplayer was the first tastemaker website. There was no Complex or Nahright or Pitchfork. It was like the first for us—the first prominent tastemaker site for hip-hop.

Questlove: Angela pretty much wrote all the updates. That’s where the real charm of Okayplayer came in. Angie was defying all stereotypes. She was a beautiful girl who had a crazy sense of humor. Even more than me, she was the one who connected with the initial class of ’99—the people who first started coming into the boards. She became the voice. She had a lively style.

Dan Petruzzi: Angela’s from deep southwest Philadelphia, one of the more dangerous parts of Philly. She was curly haired, super intelligent, and really, really funny—that was her most noticeable asset. Okayplayer was built on comedy—the blogging early on, was built on comedy and practical jokes and she was great for that. And you know, I don’t know how she met Ahmir, but she had a blog called “The Broke Diaries,” that was hosted at the University of Pennsylvania, and it got some attention because the writing was really good and the stories were hilarious.

BUILDING THE TEAM:

Doug Muir: I'm from Toronto and my day job was a web designer. I was always a big Roots fan and I had them on this ridiculously big pedestal. I found out that this Okayplayer stuff was starting, and I went to the site one day and I saw that it looked like shit. I was like, “Come on—this is the legendary Roots crew! You can't have a website that looks like shit.” I sent them an email one night when I was bored that said something like this is a disgrace to The Roots or some shit like that. I said I'll design your homepage for free if you contemplate changing the shit.

I redid the homepage with some sort of vintage Blue Note kind of thing. I'm kind of a creative-slash-digital person—I do the coding as well as the design stuff. So I designed this vintage album cover with Black Thought on it and I coded it so it was HTML ready and I sent it to them, like, Please, just put this shit up. Apparently they liked it so much that Angie flew to Toronto. I showed her around the city and we hit it off and became friends. She went back and she was my advocate to say we should bring this guy down, he does really good work.

It was just a bunch of people pulling ridiculous, ridiculous hours, eating cheesesteaks at 3 in the morning, cranking out artist website after artist website while maintaining Okayplayer.com. —Doug Muir

I had my own business at the time and I ended up telling my partners you guys run this shit for a while. I'll try to contribute where I can, but I gotta go to Philly. So I packed up and moved to south Philly. I was staying in Malik B's old apartment, which was two doors down from where Ahmir lived. So i'm like straight up 215. I'm not a big dick-rider but i had The Roots on this ridiculous pedestal and i now live in Philadelphia and am working with them.

It was just a bunch of people pulling ridiculous, ridiculous hours, eating cheesesteaks at 3 in the morning, cranking out artist website after artist website while maintaining Okayplayer.com, keeping it fresh with content, reaching out to the community on a regular basis, getting them to contribute, and helping everything to grow and evolve.

Dan Petruzzi: I lied on my resume and said I knew Flash. I applied and the next morning I went to Barnes & Noble, got a tutorial book, went home and just ran through it in four or five days. It was pretty fun and easy. By the time I was done, I emailed them back and checked in with them—I felt a little more confident then.

The interview was on 421 North 7th Street in Philly, same address as the Electric Factory. We were right below one of the premiere studios in Philly. Everybody recorded there—it was The Roots' office. It was management, production, all their tour gear was stored in our office, and we ran our website out of the office too. It was a very independent operation. Things Fall Apart had just come out. They had just won a Grammy for “You Got Me.”

I met with Doug Muir—the original IT person and designer, a Jamaican cat from Toronto. Really cool guy. He set up all the servers in the office and had done all the coding for Okayplayer up to that point. I got the job and I started four days before my 24th birthday in April of 2000. The next day we met in a conference room in the apartment complex Black Thought lived in. He lived in a building with a doorman that had conference rooms on the ground floor. Everyone had their StarTACs and their Motorola two-way joints.

Everyone was laid-back, but was really good at what they did. There was a feeling of purpose when we were there as far as starting the company and blazing your path in the new media space. It was pretty much open territory, so that was a motivator.

People didn’t know what to think of us. Everybody would say, you’re a website, you’re a record label, you’re a managment company. They didn’t really know what it was, because we had our name all over the place—on fliers, posters, CD trays, on CDs themselves, on albums that were coming out on major labels. So people didn’t know what Okayplayer was. I always thought that helped us.

THE BOARDS

Shawn Gee: Another thing that Ang added on, which I would say was the second greatest decision in the early development of Okayplayer, was she added message boards. With those message boards, the fan had a voice, so it wasn’t just Angie, Ahmir, the Roots, and a one-way communication. When we put up the message boards, the first people we had come in and identify themselves were Roots fans, obviously. But what we started to see in that second wave was that some of these people were just individuals who were expressing themselves and communicating with other like-minded individuals. They had found a home.

Questlove: The early vets—anyone there who has over 35,000–90,000 posts—a lot of them had that, “Is this really you?” type of thing. That left real quick once you showed that you’re human. That’s the important thing; I wanted a place where I could learn stuff. The way you get to be known as a smart cat is that you got to surround yourself with people who know more than you do. You take from them and you become smarter.

Shawn Gee: Questlove’s a communication junkie. Pre-Internet, he had a cell phone, and in each city of the tour he would change his outgoing message so depending on the city he would have different artists on there. People would call him not to talk to him or to even leave a message but to hear where he was and see who was on his voicemail.

No one wants to feel human in hip-hop. Everyone’s whole goal is to rise above the ashes and become superhuman. I was doing my best to try and dispel that myth. —Questlove

He communicated directly with the fans. Initially there was a bunch of fandom type of questions that fans ask artists but eventually he became a regular member who joined in on regular conversations. People would argue with him, people would disagree with him.

Questlove: I would get into the posts and the boards and basically strip down and become human to the point where I was a regular cat. No one wants to feel human in hip-hop. Everyone’s whole goal is to rise above the ashes and become superhuman. I was doing my best to try and dispel that myth, to normalize myself in ways where they feel comfortable with it. Most people would be delusional to think that it would happen, but I like to think it was a place where I could become human.

Doug Muir: Ahmir is super digital dude and was always up on the forums. So it was a place where if if you were a Roots fan you could basically talk to Questlove and see what the band was doing. That brought in a lot of like-minded hip-hop fans to one digital space. It was like a social network before people had the term social network for that sort of thing.

Shawn Gee: People were discovering this web community called Okayplayer, but they may not have even heard of The Roots. They connected on the message board, not even about music, not even about art, but about life. What school should I go to? College applications, your girlfriend—I broke up with my girlfriend. It became less about the art and more about every day issues. General discussion is just that. It could be, Hey, I went to a club and fucked three girls. Or, Did you guys see the Grammys last night?

The sports forum was my idea. I’m a sports fanatic and there were sports conversations happening in general discussion. I’m a private person—I’m not the type to talk about what’s going on in my life. But when you’re talking about the game last night and who you think is going to win the Cy Young award or whatever, I would engage. When we had our strategic meetings, I would say, we should break that off as its own forum.

There was a forum called the Left, then there was general hip-hop discussion. Then we started realizing we were getting a lot of people who are interested in technology who want to have a higher conversation about tech. So we built a tech forum. It grew out of what was happening on the site. That’s one of the things we did very well: We watched, listened, and reacted very well to what was happening on the site.

Dan Petruzzi: I started the tech forum. That’s the last one we added. It never took off like the music discussion forum, but it’s there.

Quest has always been very involved with the message boards and he’s one of the biggest reasons why they are what they are, because he’s an expert on music and he’s very opinionated and very knowledgeable and he has a lot of stories and he likes to write.

We interviewed Kanye right before “Through The Wire” came out and that interview lives on the message boards. We didn’t even have a section to post something like that. We never set out to be a publication. Just like I had to teach myself Flash I had to teach myself content too. A lot of stuff we’ve been figuring out as we go.

Questlove: Friendships that I have to this day are from people who I started having differences with. FWMJ is a good example; he runs Rappersiknow. He did a scathing review of Phrenology—that was a major moment for the site where someone isn’t supposed to drink the Kool-Aid. It’s a place where you are really honest about how you feel. That was a moment.

And no one does better BET Awards commentary than Okayplayer. I tested my theory last year and didn't even watch the BET Awards. I just read the 600-thread count on Okayplayer and that was enough for me.

THE ARTISTS

Questlove: The one who came up with the idea of becoming bigger than just a Roots website was actually Rahzel. He had come over to the house to see Okayplayer because at the time, he was working on his solo record. He wanted to do some exclusive stuff for the site. He’s telling me, “I’m all aboard, but you know what it should be? Okayplayer shouldn’t be your home. It should be a mall. You own all these malls with empty stores. And you’ll get a Rahzel store, and next to him you’ll get a D’Angelo store. Then you went and got an Erykah Badu store, and....” He kept going on and I was like, “Holy shit. I could do that.”

Shawn Gee:OK, we hired an individual on payroll, we bought a computer, there are expenses associated with running this sort of thing. As a business man I was asking myself, is there some sort of business model that could offset some of these expenses? Because in those early years there was no Jimmy Fallon and there were no large Roots shows. We were struggling to survive show in and show out.

I was asking myself, is there some sort of business model that could offset some of these expenses? Because in those early years there was no Jimmy Fallon and there were no large Roots shows. We were struggling to survive show in and show out. —Shawn Gee

Why don’t we go and market what we have to other artists? It’s a community of like-minded individuals that developed organically. We thought that if it was interesting to us, it would be interesting to others. So we reached out to a number of artists we already had relationships with. We reached out to Common, we reached out to D’Angelo. Those were the first two artists. We had a relaunch of Okayplayer which included the web presence for multiple artists. So now you have the D Angelo fan, who’s thinking Voodoo’s coming out. Where can I go to get some information?

Questlove: There was this joke about Okayplayer being my ant farm. It was my ant farm for two years. Then once D’Angelo came aboard, and he was active in his career, that’s the point in which we started crashing the servers and hosts and hosts and hosts. I remember we always had problems with overcrowding and crashing our hosts.

Labels started to approach us to build sites for their artists. That was to keep the lights on. It was funded out of my pockets and whatever merch we could move, and the icing on the top was doing work for other labels. Like Universal would always come with an artist that wasn't necessarily Okayplayer-related, but they liked the formula that we had built. So my concern primarily for the first ten years was definitely, "Let's just keep the lights on."

Dan Petruzzi: Analytics didn’t even enter the equation until way later. We had stats, but we weren’t selling traffic at the time. We knew how many people were on the boards and how many people were on concurrently. We’d look at those numbers and it was popping. But a lot of times when you run a website you have tunnel vision. You’re not really looking at other people’s stuff too much. You have a job and you know what your job is. Our job was to land these deals with labels and artists to create this community. You had all these artists who had substantial fanbases but were still “underground” but when you combined these collective fanbases it became very substantial. And there wasn’t anyone doing what we were doing, so it felt very unique and progressive.

Shawn Gee: Once we saw that it was bigger than The Roots, Common, and D’Angelo we started expanding. We started that cross-pollination on the artist side as well and built Okayplayer into a hub. That was the home of left-of-center music in urban culture at that time. You started to see other artists come under our umbrella, but even on our message boards, you started to see artists who weren’t part of our core, but were part of the community.

We saw everyone from Will.I.Am to Jill Scott. Phonte and Nicolay, they met on our boards—Foreign Exchange was born on Okayplayer. The cool thing about the community that we built was that you started to see how things were built and developed around an idea. Great minds and great elements that came together.

Dan Petruzzi: At the time The Roots were popular but they weren’t making a lot of money. Same for Common, same for Black Star. D’Angelo was a little more successful. Voodoo had been doing well. So it made total sense to try and pitch the labels and the artists to be part of this thing where we could all share the same resources—which is community, e-commerce, news updates.

Our job was to promote them 24 hours a day. And it was limited to those people. That was originally the model, and we were getting artists to pay us. For every release we would customize a website around the album artwork. On the Voodoo promo and on the tray card in the cd case it says, okayplayer.com/dangelo. That was the official website. Same with Like Water For Chocolate. The websites all lived on Okayplayer, but they had their own entry points. We’d keep them updated with a photo gallery and news updates and we’d also blog about the different happenings on our homepage. We did it in a way where it cross-promoted the different artists. Obviously, our model has changed a lot since then.

Questlove: It’s such a common thing now for artists to be on Twitter and Facebook. But the idea of a velvet rope was still a thing back in the late ’90s. [There wasn’t] a lot of access to a person’s life. Pretty much the only people that were open to it were the people I was working closely with. I would start a post on Okayplayer and just keep the computer open all day and go live no matter where I was.

I would go shopping with Zack de la Rocha, talk about it in the post, and go live with it. One day I remember Zack wanted to work on the solo record and we went shopping and we both came back with 300 records between us. We spent all day listening to the records, and cut for cut, I would write the cuts we’re playing and the reaction. “OK, we’ll listen to ‘Inspiration Information’ by Shuggie Otis... Oh yeah, this is cool. Maybe we’ll work on this or loop this or try to sample that.” Stuff like that.

Dan Petruzzi: Questlove brought the other artists who still hadn’t figured out how to communicate with fans on the Internet. Back then rappers didn’t have computers, and they didn’t care to. For most of these dudes from south Philly and The Roots, they had no interest in being on the Internet. They made music.

Back then rappers didn’t have computers, and they didn’t care to. For most of these dudes from south Philly and The Roots, they had no interest in being on the Internet. They made music. —Dan Petruzzi

Like Black Thought—it just wasn’t up his alley. He tried it a couple times because Ahmir got him to, but he was not into it. Kweli was always into it, Mos not so much. He was never really into it at all, actually. It wasn’t D’Angelo’s thing. It wasn’t like he didn’t like it; it just wasn’t his thing. Then there were people like Skillz that got busy on their own. Erykah’s really proficient with it now. She’s an analog girl in a digital world—that’s her handle on Okayplayer.

Doug Muir: I have Black Thought in my top 5 lyricists of all time. i had the idea that being able to work with him would be cool. But he was on some, “Fuck these Internet nerds.” He was like, “I don't give a shit about any of this.” So any time we needed him for anything, it was nearly impossible. He was not down with us. He wasn't against it. He's just a really private person. He didn't get why people were online talking about hip-hop. And to this day he doesn't use Facebook or Twitter.

Questlove: Some of the artists I worked with took an interest in it. Erykah Badu would always be like, “Tell them this, tell ’em that.” D’Angelo just shunned the idea.

I was real close to getting Jay-Z aboard. When I was mastering Unplugged, he was there basically for the process of mastering and was always wondering why I had my computer everywhere I went with me. He’s like, “What are you doing? What are you typing?” He seemed really impressed with the real time instantaneous responses he would get. I know there was a thread I put up about “Mastering with Hov” in real time. Jay says, “What up? What questions y’all got?” He maybe answered like four of them.

Things were that way for Kweli. Despite his lack of participation, Mos seemed to be into it as well. That’s how we were able to pull people in. They saw the kind of camaraderie we had with our fanbase and it makes you want a piece of the action. I guess we were the Pied Pipers of that movement of the second half of the ’90s.

THE OKAYPLAYER HATERS

Talib Kweli: I didn’t even own a laptop until 2004. It’s not like that anymore, but from the beginning Okayplayer was centered around the artists. So whether or not I was on the Internet I was part of the movement. You had a Talib Kweli tab and Reflection Eternal tab, along with Common and The Roots, Slum Village and a bunch of other Okayplayer artists.

Common: I remember not being very tech savvy and Questlove was always ahead of the game when it came to that. I remember him trying to get me on a chat room and we did it. He would type the thing and get responses back and I remember being frustrated. I had these guys commenting on the music we need to do. I had to get adjusted to that world. I was used to fans interacting in person and giving an opinion. Or them coming up to you and telling you, “this is what I think.” So fans expressing themselves through the chat rooms, it was new for me.

Man—these cats can sit behind the computer and say a lot of stuff that they won’t say to your face at all. It’s not like he say it to my face and we going to fight. It’s just like having the heart to say something to somebody and look them in the eye, you know?

Questlove: Me and Angela had a proud parent moment. This is when we were making Like Water For Chocolate, and I suggested to Angela to come up to the Electric Lady Studios. By this point we had an airtight system at Electric Lady. D’Angelo was in studio A, Common was in studio B, studio C upstairs was like an associated artist. Mostly Kweli, sometimes Mos, sometimes Bilal, or just someone that was family associated. D’Angelo always came late at night, so Erykah would take his daytime hours to start working on her records. Electric Lady Studios at one point became like Okayplayer central.

Man—these cats can sit behind the computer and say a lot of stuff that they won’t say to your face at all. It’s not like he say it to my face and we going to fight. It’s just like having the heart to say something to somebody and look them in the eye. —Common

I suggested Angela come down to seal the deal. I knew I had Common, but I figured a real cute girl... He was going through that phase where different educated women, that really got into his ear. So I was thinking OK, let Angela come in, pitch it to him and we got him.

To really make the offer sweet, I decided to give him my very first computer, because at this point I had graduated. I was using a Sony PC because they have better speakers. So my very first computer, maybe it was a HP—I’m not certain, but it was OK. And even when he agreed to join Okayplayer and do some marketing with the website, we could not for the life of us get him to be an active participant. To this day when I ask, I think his computer is still sitting in his momma’s basement in Chicago.

Common: It was honestly just that one time with Quest and I didn’t really take to it well. I didn’t like it. I was just like, “Y’all do that.” I remember him wanting us to be consistently present with that. Quest understood the value way before I did. But I don’t really go on the site at all. I pretty much stay away from comments about music and just keep creating. I check certain things here and there. I like to stay in tune wit what the fans are into and what’s dope to me, but put it this way—it’s very rare that I go on many blogs or sites.

Questlove: Erykah was the same way. She was allergic to the Internet. I always thought it was a fear of… You know, I’ll get you a computer. If you’re scared, if you don’t know how to turn on the power or whatever, I’ll get somebody to teach you. I think one day Erykah said that she just got tired of being left out. Rashad Smith was working on her record, and Rashad had his computer setup—he had two of them. Then James Poyser had his computer setup and I had my computer setup. Like, everybody was having fun with computers. She just decided, “Well, I want to get in all the fun.” She finally jumped in the river—albeit a little late, like around 2004. Better late than never. But she definitely was one of them people that was scared of the Internet. And it’s a scary thing. When you throw them in the lake, they’re trusting you to throw them in the lake but it’s like, Oh, I forgot to mention there’s a few piranhas in there—but don’t mind them. They don’t mean you no harm.

You definitely need tough skin. Because I’ve been there from the beginning, having Okayplayer has definitely prepared me for snark elsewhere on the Internet. You got to know how to pick and choose your battles with the Internet. Most people that do snark do so as a means to make a mark. True hate and truly disliking something is actually to ignore it. Nothing against One Direction, but I have no interest in their music. It’s just nowhere in my stratosphere. It’s nowhere on my radar. And that’s a true example of not liking something. But when you go out of your way to take that piñata and try and bash the shit out of it, that’s a whole other story. That’s the thing that you can’t explainto people.

Me and Mos, we had a problem, where maybe for like four or five months we didn’t talk. He didn’t like it, but I had to be honest. That was just like the early moments where honesty and artistry clashed. —Questlove

I remember once, man, Mos got heated at me. I took the real-time diary to the next level when we started the Voodoo Tour with D’Angelo. Every day I basically kept a journal from the beginning of the Voodoo Tour, from March of 2000 all the way from my very last day in Atlanta in October of 2000. And all the stops, I was painfully honest about the whole experience. When me and D’Angelo had arguments, I Iet people know. I’d rate the show by “@” signs, so a classic night was a five; mediocre night was a three. And I was honest about everything.

I wrote about cats being late for lobby call, D’Angelo included. But the thing that really got me in trouble was just the conflicts that Mos was having in his position as the opener. He was chosen because he was the man, he had incredible stage presence, he had the album, and he was a very engaging performer. But there would be the cases of him not wanting to go on because there was nobody in the audience to perform for. He thought it was too early or that type of thing. When you’re the opening act, this is what you deal with. I’ve played houses with seven people, eight people, most of them bartenders and barmaids. And D’Angelo is an artist that likes to show up fashionably late.

I was just being real. Reality serves you one thing, but I guess it’s a whole other thing to really keep a live journal about things. I wanted to keep it honest without being disrespectful. Me and Mos, we had a problem, where maybe for like four or five months we didn’t talk. He didn’t like it, but I had to be honest. That was just like the early moments where honesty and artistry clashed.

Talib Kweli: My introduction to Okayplayer was a warm family thing: Here’s all these artists, this community. It’s all warm and fuzzy. We support each other. And then when it got to be a little bit more bitter, I was confused by it.

Some people really didn’t like the creative choices surrounding [my album] Beautiful Struggle. Before they even heard the album there was a lot of negativity surrounding it. And then for me to respond so negatively when it leaked, that didn’t help me at all. That actually turned a lot of people off, because they felt like I was attacking them rather than trying to defend my art.

Dan Petruzzi: I once got a four-page fax from Kweli from a hotel room. I don’t remember what it was about. But he wrote it out, went to the business center in his hotel room, and faxed it to me. I had to type it up and post it on the forums as him.

Shawn Gee: We opened the door of direct communication to the fans, and artists learned a lot. Before that, there was always a third party between the fans and the artist. What Okayplayer did early on was open that direct communication, sometimes for the good, sometimes for the bad. Some artists communicated and all was fine, but some—and I won’t place blame on the artist—but sometimes that communication turned negative when fans were being critical. A lot of times the artist would run away, or would jump off, or would react negatively. It was a gift and a curse.

Talib Kweli: I wasn’t Internet savvy at all. I am a lot more Internet savvy now than I was back then, but I was from a different generation where the way that you deal with artists, you come with a little more of a respectful tone. I just didn’t understand the language of the Internet or the culture of trolling, the culture of people just saying wild shit just so they can get hits on their blogs. I didn’t understand any of that, and to me I treated that like you would treat anybody in a face-to-face situation.

There was an Okayplayer member who had leaked my album or participated in the spreading of the leaking of my album. And I kinda went off on this kid in the message boards. —Talib Kweli

Questlove: There’s another side to this coin which is basically you got to maintain your cool. I’ll probably go at one or two cats if they’re being really ignorant. I always had this thing where they could smell blood in the water. Maybe I got halfway through it and then decided not to read the rest, or nor read the responses. And that’s the thing that just amazed me. Because didn’t Talib put that on Kanye’s record? “Always got something to say like an Okayplayer hater.” Shit, I just found out Jill [Scott] dedicated “Hate On Me” to Okayplayer as well [Laughs.] We’re some horrible trolls aren’t we?

Shawn Gee: There was a song with Kweli, Kanye, and Common where Kweli says something about being an Okayplayer hater. You started to see how Okayplayer was impacting the artists. It began to make its way into the songs. Jill Scott had a song called “Hate on Me” and I saw a thread back when it came out where they said one of the reasons she wrote that song was because she was another one who was more of an analog person that wasn't heavy on the web, and when she got involved she received some hate. There was some negative back and forth.

Common: I knew Kweli had been through some disputes with people on Okayplayer and he expressed himself. I think freedom of expression is important. If somebody says something to you, you have to be able to say something back. So I understand where Kweli was coming from and he was fighting a specific group of people who talk shit and really have nothing good to say.

Talib Kweli: There was an Okayplayer member who had leaked my album or participated in the spreading of the leaking of my album. And I kinda went off on this kid in the message boards and that wasn’t the venue for me to be going off. I felt like everything I was saying was right but I didn’t take into consideration the context.

I’m a lot more clear on it now but back then in 2004 I was just confused. After I saw the power of that community and after I saw how passionate they were about music, I started to engage the Okayplayer boards. I started to realize part of my problem with this community is that I’m not actively participating in it. That’s why I don’t understand it. So I started to post stuff, then it all kinda came full circle a year later, two years later when I put out Liberation. A lot of Okayplayer message boarders who thought I took a wrong turn with Beautiful Struggle or thought I took a wrong turn with that letter that I wrote, started to come back into the fold. It took me two years to figure out, “Oh you guys just want free music.”

That whole anonymous-ness, that whole "I’m going to make up a name and just say the wildest shit," is just intriguing to me. But I had to realize that that’s what happens. It’s not Okayplayer. It’s the Internet. As an artist you have an ego and you’re paranoid wondering why people are talking about you or wondering why people aren’t talking about you. So sometimes as an artist you go online to stoke your own ego. There’s really nothing to gain from people lavishing praise on you or people teaming up against you.

Shawn Gee: When some artists came on, some members would say things like, “That was the worst album you ever made!” And that artist would either react in the same level of extreme description or they would sign off and not come back. if 95 percent of things are positive and 5 percent are negative, you’re goin to focus on the negative. That was the gift and curse of the artist communication. What we started to see was, there were a lot of artists who were part of the boards who did not sign on as themselves. You had a lot of lurkers. They appreciated the communication and they appreciated the medium, they just didn’t want to get thrashed by the rest of the community. They just wanted to hang out and talk shit like everyone else.

Talib Kweli: I still go on Okayplayer fairly frequently, but I don’t spend as much time on it as I used to. I just kinda go on to see that they’re abreast of what I’m doing, but I used to really spend time addressing stuff on there. I went on the message board and there were two messages about me. These were the only two there. This was like a month ago, right? One was basically saying, you know, “I hate Kweli, I hate everything he’s done since Blackstar, but you know what? This Attack the Block is pretty damn good.” That was a perfect comment from Okayplayer. And the other comment I saw was “So has the random Kweli hating stopped yet?” Which made me feel like “Yo I wasn’t that paranoid.” It was just random people [who] had it out for me. For people to ask if it had stopped yet means that it was happening.

Questlove: The Internet offers people this anonymous platform to become their own Robert Christgau or their own Lester Bangs. I can’t defend it nor condone. That doesn’t mean that I’m being noncommittal about it. I get it on both sides, which is why usually when I turn in a record I’m always thinking about, how bulletproof is this? And the bulletproof I’m talking about ain’t Pitchfork-bulletproof or Slate-bulletproof or Rolling Stone record review bulletproof. I’m normally thinking about Okayplayers first because in my head, it starts there. And if they come at you piranha-style, then I feel like the rest of the journalist community will always take cues.

But then that sort of a cultish action thing can also have a backlash. I’ll go to other websites and read about how Okayplayer is like a kind of cult, lynch mobs of the Internet, that type of thing. I’ve seen [Pitchfork’s] Tom Breihan, I think that’s what he called it, like a cult center. That’s kind of a double-edged sword.

THE MEET-UPS

Dan Petruzzi: My first year on the job they had the first reunion. They called it a reunion even though it was the first one. And that was in Philly and we played laser tag and Angie was very much involved in organizing it. I think we went bowling too.

Questlove: The very first reunion, I remember Angela was like dead-set against us endorsing it or really having something to do with it. Just for like legal reasons, because a lot of these people would do stuff in the name of hip-hop. But they were still underage and whatnot.

I remember that they had the very first reunion in Philadelphia and I know that she wanted us to keep our hands clean of it, but I couldn’t. I remember this being one of the first major conflicts that Angela and I had over the site. I couldn’t do that. I don’t know if I was enjoying the spotlight or whatever

I decided that I was gonna treat everybody to laser tag. What The Roots would do, pretty much our daily routine was we’d go to work around like one in the afternoon. We’d stop at ten at night. Usually me and Scratch, we’d go play pool at the pool hall. Some nights we’d all go play laser tag. That was just how we relieved stress and all that stuff. It would just be like 12, 14 of us and the place would stay open until like midnight, one in the morning. We’d all just go laser tagging.

The first reunion, there had to be at least 76 people. That was just amazing to me the fact that 76 people came from all parts of the U.S. to meet each other for the first time. It’s weird that a lot of those friendships, people I see now, people that are now in their late thirties, early forties, those friendships were started on the website. —Questlove

The first reunion, there had to be at least 76 people. That was just amazing to me the fact that 76 people came from all parts of the U.S. to meet each other for the first time. It’s weird that a lot of those friendships, people I see now, people that are now in their late thirties, early forties, those friendships were started on the website.

The night that we recorded The Roots Come Alive, there was a girl who didn’t want to miss this, I think she was 16 or 17. I don’t how she swiped her mom’s credit card to get a plane ticket. Whatever the case, the plan got foiled and her mom stopped her from leaving. She was like crying and throwing a fit. So she had written somebody at the site like, “Can somebody send signed drumsticks to my daughter? This is all she’s crying about.”

So, I sent the drumsticks and I had reached out. I inboxed her or thought I was inboxing her on the site. Like, “Okay I sent your drumsticks. Sorry you missed the show.” And she was like, “Oh that wasn’t me, that was dadada.” Then I apologized. I was like, “My bad, forgive me. I’ll talk to you later.” But soon we became friends and, like, an item.

TalibKweli: The Okayplayer tour that I went on, that tour changed my life. Two months of touring with the Roots and Gang Starr and Slum Village and all these people, it really put me on that community and I gained all of the Roots fanbase by doing that tour. Like everyone who was fucking withOkayplayer started fucking with Reflection Eternal heavy around that time.

Questlove: When did I know it was getting big? I'll probably say the Okayplayer Tour of 2000. That felt like a moment. That's when Sean first reminded me, "Yo man, this started in your bedroom." And it was such a big moment. We were doing the encore which was "Hip-Hop" with dead prez. Slum Village was on stage, Common had come by. Erykah, she popped in. This big-ass Okayplayer sign sitting behind me, dead prez is unsuccessfully trying to light a flag on fire laughs and the whole place is jumping. I even think Chappelle was there. He witnessed it.

I'm world famous for not enjoying the moment. Like, I abhor the idea of celebrating the idea of, "We me made it! We made it!" because it's always an up-and-down moment, but that was when I realized, Okay, this is special. We have a community, we have something special here.

It’s weird that Okayplayer was the precursor to how we know the Internet now. Businesses were started with people. Babies have been made. Marriages. Groups, The Foreign Exchange. This is much more than, “Hey guys I got this new record out called Phrenology and I hope you guys support me.” It’s never been about that. As a matter of fact, I’ve stopped giving Roots updates of studio announcements because it’s not even about that anymore. If I start doing that like, “Hey guys, the new album is called Undun.” The typical reaction would be, “Psh... Motherfucker get out of here with that shit.” But it’s still like their home.

THE NEXT LEVEL

Questlove: Now we're in a place where we're a little bit comfortable. We've survived every promise. In '99 and 2000, 2001, it was all about the Internet boom. "I heard this cat sold his company for $10 million, what's up with that? Where's my money?" There was a lot of that. I'm actually glad it didn't happen. It would have been easy to sort of go the route of how many companies went, from being a boutique shop to a chain.

Like the deal we almost did with George Jackson. That was a major life lesson. If you go back to that whole Internet boom time, everybody was going to invest money. George Jackson, one of the producers of New Jack City was working at BET at the time, like an executive at BET, and he really liked the site and he wanted to invest in buying it immediately.

D'Angelo had probably brought us our biggest non-left-of-center audience. The urban audience, conservative to the right, closer to the UPN/CW/Tyler Perry side of things, as opposed to what we represented.

So this was like a Thursday. It's like, "Well, we made a deal. Congratulations Mr. Thompson." Just go back to those Wayne’s World dream sequences imitates dream sequence sound effect where it's like OK, now you see me in the back of the car, Flavor Flav white top hat, tuxedo on, burning $100 bills with a cigar [Laughs.] I'm just dreaming, like, "Oh my God man, this is coming true." Like, the soundtrack in my head was "Hypnotize"—that's the song. A helicopter landed on my yacht to take me away to Mexico or somewhere.

Man, oh man—the meeting was Tuesday. We were going to sign on the dotted line. In my lifetime I'm actually going to hold a check that has seven figures on it. I can't wait! And that Tuesday, George died.

You see me in the back of the car, Flavor Flav white top hat, tuxedo on, burning $100 bills with a cigar [Laughs.] I'm just dreaming... Like, the soundtrack in my head was 'Hypnotize.' A helicopter landed on my yacht to take me away to Mexico or somewhere. —Questlove

That let all the air out of the balloon. And it was just like, man, we're going back to the little train that could. This was back when production with The Roots was all I had. There was definitely some weeks where it was like, OK guys, look, I know… To work in a place with just four white walls and no windows? There are definitely some feuds that are going down.

A lot of arguments went down, a lot of non-amicable exits. We're all adults now so we've since then kissed and made up. Especially back then with the lack of technology, you would have to be there on-call almost eighteen hours a day. Wanting to post something at nine o'clock and the server goes down. I'm having a heart attack like, "Yo, what the fuck!" Then someone has to drive all the way back to Philadelphia just to fix some code. You had to be a doctor on standby. It's not easy being part of a five-man team for a job that really requires 20 people. And in an environment with no windows and less than human conditions, but my pockets couldn't afford it at the time.

Now we're definitely in a way better place. We've kind of nuanced Okayplayer from being an artist website. It's still a musician’s community, but it's open to music. I didn’t know ten years ago there would be this much attention on electronic music. Like what Skrillex is up to or what Diplo is up to, that type of thing. Whereas back then, it was specific. You could only talk about Common, Dilla—like very specific things in the hip-hop parameter. We kind of transcended that and to fine effect I believe.

I don't know if it was by force or by choice, but we stayed a boutique shop and stayed steady throughout the storm. There's been a lot of moments where it's like, "It's over for us," and then something changes at the last minute. In general, people's interest in music doesn't die. As long as we have that then we're cool.

Okayplayer's job is to be the soapbox for the unheard. I trust and expect more groups to start in the vein of Tanya Morgan and Foreign Exchange. I expect vets to grow out of it, I expect veterans to still stay there and sound like grumpy old men because they like this Premier beat better than that Premier beat. And then someone under it says, "Who's Premier?"

Common: At the end of the day I’m connected to them and connected to the movement, like we still family. If they are doing things involved with Okayplayer and I’m asked, then I’m there because it was there from the beginning, the present and the future—no matter what because that’s my family. The Roots are my family and that’s the community they established so I will always be a part of that.

Talib Kweli: I definitely had my negative experiences with one entitled Internet culture and two with my own ignorance about what that culture meant. But no matter what happened on the message board, me and the people who run Okayplayer have always had a fantastic relationship. I don’t hold them responsible for any of that nonsense that I went through. They’ve always supported me and I’m always going to support them. Okayplayer has always been there for me and that’s part of my story as an artist.

Shawn Gee: Dan Petruzzi worked his way up to the chief. He’s the one that runs the day-to-day and he made the decision based on what was happening in the business, with relationships, and access to sort of move the company from Philly to New York.

Dan Petruzzi: The industry changed, we maybe may not have even realized the ways in which it was changing, but we moved fluidly with it. Labels started building new media departments in house,, they started figuring out what new media was. CDs were still selling at the time and Napster had changed things, and affected sales at the time, but Napster got shut down, the iPod wasn’t out yet. At the time we had the ability to influence how certain record labels rolled out certain records. Because they were open to experimentation. They still are, but not as much.

Shawn Gee: As the company grew, individuals grew, Angie left the company and got a book deal. I don’t think the book deal was directly related to Okayplayer, but once she was in discussion with the publisher she pointed to some of things she was doing on Okayplayer and they saw that as a real positive. So she got a book deal which morphed into a development deal, which morphed into her moving to California, which morphed into her becoming a head writer on Scrubs.

Questlove: We've all moved to New York. I guess the name of the game is community and growth. It's interesting. It doesn't have to be about, like the seed of it starts of course with Hip-Hop and a Hip-Hop band. But it's like we all grow up. Now it's used as a means for LargeUp and OkayAfrica. Its many offsprings. It's slowly growing. I'm just glad it's there.

And it's kind of weird. I thought I had the upper hand on knowing what's going on. I use OkayAfrica, like I use my own company so I can find out what interesting music is going on. And I'm still jaw-dropped at the fact, like, “Wow, this happened and this happened and this happened” and me not having a clue. I need Okayplayer. I go in there and I click, "Oh damn, I didn't know about this person. It keeps me sharp. If it grows, it grows, but at the end of the day that's what I expect it to be. A playground for the unheard. I need it more than it needs me. That's probably the bottom line right there.